Benzenepropanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methoxy-, methyl ester, (S)-

Base Information

• Chemical Name: Benzenepropanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methoxy-, methyl ester, (S)-
• CAS No.: 96363-21-2
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• DSSTox Substance ID: DTXSID901118772
• Mol file: 96363-21-2.mol

Synonyms:DTXSID901118772;96363-21-2;Benzenepropanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methoxy-, methyl ester, (S)-

Chemical Property of Benzenepropanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methoxy-, methyl ester, (S)-

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 369

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)OC)C1=CC=C(C=C1)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC(=O)OC)C1=CC=C(C=C1)OC

Technology Process of Benzenepropanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methoxy-, methyl ester, (S)-

There total 10 articles about Benzenepropanoic acid, beta-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methoxy-, methyl ester, (S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

methanol (67-56-1) + D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)propanoic acid (96363-20-1,500788-87-4) → methyl D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)propanoate (96363-21-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1021/jo00213a012

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → methyl D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)propanoate (96363-21-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / ammonium acetate / ethanol; H₂O / 13 h / Heating

2: 88 percent / 1 N NaOH / dioxane; H₂O / 1.) 0 deg C, 10 min, 2.) RT, 3 h

3: 87 percent / 4-(dimethylamino)pyridine (DMAP), dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 12 h / Ambient temperature

With ammonium acetate; dmap; sodium hydroxide; dicyclohexyl-carbodiimide; In 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1021/jo00213a012

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 3-amino-3-(4-methoxyphenyl)propionic acid methyl ester (131791-82-7,227319-36-0) → methyl D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)propanoate (96363-21-2)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 80 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.08.099

upstream raw materials:

methanol

D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)propanoic acid

4-methoxy-benzaldehyde

di-tert-butyl dicarbonate

Downstream raw materials:

D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)<1-2H>propanal

(1S)-D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)<1-2H>propanol

(1R)-D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)<1-2H>propanol

(1S)-D,L-3-<<(1,1-dimethylethoxy)carbonyl>amino>-3-(4-methoxyphenyl)<1-2H>propyl propanoate